Santalol ether.



UNITED STATES rrrrnn r orrion.

'J'IITRGEN OALLSEN, OF E'LBERFELD, GERMANY, ASSIGNOR TO FARBENFABRIKENvoRM.

' FRTEDB. BAYER & co, or ELBERFELD, GERMANY, A CORPORATION or GERMANY.

SANTALOL ETHEB.

To all whom it may concern:

Be it known that I, Jtinonn OALLSEN, doctor of philosophy, chemist,citizen of the German Empire,- residing at Elberfeld, Germany, Kingdomof Prussia, have invented new and useful Improvements in Sa-ntalolEther, of which" the following is a specification.

My invention relates to the production of new pharmaceutical products,which are chemically ethers of santalol from oil of santal and whichaccording to my researches possess valuable therapeutic properties,being useful substitutes for santalol without the intense anddisagreeable taste and the irritating symptoms caused by this com pound.They are especially qualified for the treatment of gonorrhea, cystitis,etc., an average dose being between from 0.2 to

' 0.0 grams.

The process for producing the new compounds consists in treatingsantalychlorid with sodium alcoholates, such as sodium methylate, sodiumethylate, sodium phenolate, the sodium compound'of menthol, etc. or byalkylating santalol. The new products thus produced are limpid liquidswhich are soluble in alcohol and ether and are insoluble in water. Theyare.dissolved by concentrated sulfuric acid with a' reddishbrown color.On heating sa-ntalol-ethers with hydroiodic acid, santalyliodid and thecorresponding alkyliodids are formed, but since santalyliodid is quicklydecomposed, splitting off hydroiodic acid, the hydrocarbon santalene isthe final product of the reaction.

In carrying out my process practically I can proceed as follows, theparts beingiby weight: 215 parts of finely powdered phosphoruspentachlorid. contained in a flask, are covered with ligroin and to thisa solution of 220 parts of santalol dissolved in 22025O parts of ligroinis added through a dropping funnel, the flask being cooled and shaken.The reaction begins at once.

-- are boiled in a vessel connected'with a re- Yfhen the evolution ofhydrochloric acid gas has ceased, 7

The ligroin is p Specification of Letters Patent. Application filedMarch 3, 1908. Serial N 0. 18,958. (Specimens.)

Patented Jan. 12, 1909.

flux condenser for 12 hours with a solution of 30 parts of sodium inmethyl alcohol. The methyl alcohol is distilled off, the residue isdissolved in ether, the ethereal solution is washed with watercontaining a small quantity of an acid and then with water until it nolonger shows an acid reaction. The ethereal solution .is then dried overanhydrous sulfate of sodium, the ether is driven off ahd the residue isdistilled in lene. The formation of'the new methylether of santaloltakes place-probably according to the following formula:

The process is carried out in an analogous manner by using other sodiumalcoholates. The ethyl ether of santalol is a. limpid oil boiling at169-1759 centigrade under a pressure of about 22 mm. and. has theformula:

The phenyl ether of santalol obtainable from santalyl-chlorid and sodiumphenolate is a limpid oil boiling at ass-241 centigrade under a pressureof about mm. and has the formula:

c n oo n -The menthyl ether of santalol obtainable from santalylchloridand the sodium compound of menthol is a limpid oil boiling at 20l210centigrade under a pressure of about 5 millimeters and has the formula;

Having now described my invention and in what manner the same is to beperformed,

liquids soluble in ether and in alcohol, insoluble in water and solublein concentrated sulfuric acid with a reddish-brown color, on

heating with hydroiodic acid they form san- 5 talyliodid, which,however, is quickly decomposed into santalene; and exhibiting Valdabletherapeutic properties, substantially as hereinbefore described. V

2. The herein-described new methyl-ether of santalol, being a valuableremedy, obtainable by the action of sodium methylate uponsantalyl-chlorid, which is a limpid c01- orless oil bein almosttasteless; boiling at 149l56 centlgrade under a 15 about-166 mm.,soluble in alcoho 'and ether,

ressure of soluble in concentrated sulfuric acid with a reddish-browncolor and insoluble in water; and which by heating with hydreiodic acidis decomposed into santalyl' iodid santalene being finally formed fromsantalyl iodid and 20 methyl iodid, substantially as hereinbeforedescribed.

Intestimony whereof I have hereunto set my hand in the presence of'twosubscribing wltnesses.

01'10 KiiNIG, WM. WASHINGTON I BRUNSWICK.

